Phosphorus oxychloride → HCID 11179346, compound

HRID 2374875Notes

Reaction equation

HRID 2374875 reaction equation
[CH3:1][C:2]([CH3:37])([CH3:36])[C:3]([NH:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[C:8]([NH:10][CH:11]([C:13]1[N:18]=[N:17][C:16]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)=[N:15][CH:14]=1)[CH3:12])=O)=[O:4].P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:1][C:2]([CH3:37])([CH3:36])[C:3]([NH:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[C:8]1[N:18]2[C:13]([CH:14]=[N:15][C:16]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)=[N:17]2)=[C:11]([CH3:12])[N:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58711944HCID 58711944, compound2×

Product 1

HCID 11179346HCID 11179346, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a similar manner as described for Example 1, 2-[(2,2-dimethylpropanoyl)amino]-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 15) (0.040 g, 0.080 mmol) in 1,2-dichloroethane (10 mL) and phosphorus oxychloride (0.060 mL, 0.64 mmol) gave 2,2-dimethyl-N-(2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]-imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)propanamide (0.0039 g) as a yellow solid. 1H NMR (CDCl3): δ8.87 (s, 1H), 8.66 (dd, J=8.6, 1.2 Hz, 1H), 8.62 (dd, J=8.1, 1.6 Hz, 1H), 7.43-7.37 (m, 1H), 7.16-7.11 (m, 1H), 6.98 (s, 1H), 6.90 (s, 1H), 6.87 (s, 2H), 3.84 (s, 3H), 3.77 (s, 6H), 2.62 (s, 3H), 1.34 (s, 9H). MS m/z 491 (M+1).

Sources & evidence

ORD record
ord-3525e009f19448c38fee03f83b49c556
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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